Ethyl bromoacetate → 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-ethoxycarbonylmethoxy-1H-indene

HRID 1741375노트

반응식

HRID 1741375 반응식
[CH3:1][N:2]([CH:21]1[C:29]2[C:24](=[C:25]([OH:30])[CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1)[CH2:3][C:4]1[O:5][C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:8]=1.Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][N:2]([CH:21]1[C:29]2[C:24](=[C:25]([O:30][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1)[CH2:3][C:4]1[O:5][C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:8]=1

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 183672371-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-hydroxy-1H-indene

생성물 1

HCID 183673111-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-ethoxycarbonylmethoxy-1H-indene수율 60.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1-[N-methyl-N-[(4,5-diphenyloxazol-9-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene (109 mg) in dichloromethane (2 ml) was added 1M boron tribromide dichloromethane solution (1 ml) at 0° C. After being stirred for 4 hours at 0° C., the solvent was evaporated in vacuo. The residue was extracted with ethyl acetate. The mixture was washed with brine, dried over MgSO4 and evaporated in vacuo to afford crude 1-[N-methyl-N-[4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-hydroxy-1H-indene (109 mg). To a solution of crude 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-hydroxy-1H-indene (109 mg) and ethyl bromoacetate (80 mg) in DMF (3 ml) was added K2CO3 (80 mg). After being stirred for 24 hours, the solution was extracted with ethyl acetate. The mixture was washed with brine, dried over MgSO4 and evaporated on vacuo. The residue was purified by chromatography on silica gel to afford 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-ethoxycarbonylmethoxy-1H-indene (80 mg) MS (m/z): 483 (M+ +1) NMR (CDCl3, δ): 1.29 (3H, t, J=7.1 Hz), 1.98-2.21 (2H, m), 2.41 (3H, s), 2.75-3.18 (2H, m), 3.78 (1H, d, J=12 Hz), 3.82 (1H, d, J=12 Hz), 4.25 (2H, q, J=7.1 Hz), 4.63 (2H, s), 4.55-4.65 (1H, m), 6.62 (1H, m), 7.15-7.18 (2H, m), 7.25-7.45 (6H, m), 7.60-7.75 (4H, m)

후처리

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe mixture was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated on vacuo
  5. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-e552b5adf36f4d9a89cd73b65f5ead74
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05972965

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